Sodium Hydroxide → HCID 14519881, compound

HRID 1455983Notes

Reaction equation

HRID 1455983 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:10]=1[C:11]([O:13]CC1C=CC=CC=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO>[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:10]=1[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86753386HCID 86753386, compound

Product 1

HCID 14519881HCID 14519881, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl 2-benzyloxy-4-methylbenzoate acid (25 g) in a mixture of THF and methanol was treated with aqueous 2N NaOH (188 ml) and heated under reflux for 12 hours. The reaction mixture was concentrated to half its volume and was diluted with water, extracted once with EtOAc and the aqueous layer was acidified with HCl to pH4. The solid which precipitated was filtered and dried to give 2-benzyloxy-4-methylbenzoic acid (yield 9.73 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe reaction mixture was concentrated to half its volume
  4. additionwas diluted with water
  5. extractionextracted once with EtOAc
  6. customThe solid which precipitated
  7. filtrationwas filtered
  8. customdried

Sources & evidence

ORD record
ord-af339ded41d34c8dbee1435c7ad3f2aa
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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