Hydrochloric Acid → HCID 86736981, compound

HRID 1659466Notes

Reaction equation

HRID 1659466 reaction equation
[Na].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1.[O:14]1[C@H:16]([CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15]1.Cl>CO>[CH2:19]([O:18][CH2:17][C@H:16]([OH:14])[CH2:15][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 146296Oxirane, ((phenylmethoxy)methyl)-, (S)- (9CI)HCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 5360545Sodium

Product 1

HCID 86736981HCID 86736981, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

Sodium (2.3 g; 0.1 mol) was dissolved in 500 ml anhydrous MeOH and to this was added a solution of 194.3 g (1.17 mol) 4-hydroxyphenylacetic acid, methyl ester in 250 ml MeOH followed by a solution of 167.3 g. (1.018 mol) (S)-1,2-epoxy-3-benzyloxypropane in 250 ml MeOH. The solution was stirred under reflux for 12 hours. The cooled solution was treated with 8.3 ml (0.1 mol) of concentrated HCl and the methanol was removed in vacuo. The crude product was dissolved in benzene and washed with 2×200 ml portions of cold 1 N NaOH solution and with H2O (1×200 ml). The aqueous layers were backwashed with benzene (2×500 ml). The combined organic layers were dried (Na2SO4) and evaporated in vacuo to give crude (S)-4-(3-benzyloxy-2-hydroxypropoxy)phenyl acetic acid, methyl ester.

Workup

  1. temperatureunder reflux for 12 hours
  2. customthe methanol was removed in vacuo
  3. dissolutionThe crude product was dissolved in benzene
  4. washwashed with 2×200 ml portions of cold 1 N NaOH solution and with H2O (1×200 ml)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-ea5a8d626e704c138671a53f8d1d5e60
Source dataset
uspto-grants-1981_12
Patent number
US04304721

Reaction notes

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