Hydrochloric Acid → HCID 13393460, compound

HRID 2309143Notes

Reaction equation

HRID 2309143 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[C:13](=[O:31])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].[BH4-].[Na+].Cl>C(O)C>[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[CH:13]([OH:31])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 13393452Ethyl 4-hydroxy-3-octadecanoylbenzoate

Product 1

HCID 13393460HCID 13393460, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound of Example 1 (1.0 g) was dissolved in 20 ml of absolute ethanol, and 0.1 g NaBH4 was added with stirring under N2 atmosphere. The reaction mixture was stirred for two hours, added to 1N HCl, and the mixture concentrated to dryness under reduced pressure to give a crystalline mass. This solid was extracted into ethyl acetate, and the extractants combined and washed with water, then dried over sodium sulfate. The solvent was removed under reduced pressure to give the title compound, m.p. ca. 75° C. ##STR9##

Workup

  1. stirringThe reaction mixture was stirred for two hours
  2. concentrationthe mixture concentrated to dryness under reduced pressure
  3. customto give a crystalline mass
  4. extractionThis solid was extracted into ethyl acetate
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-42ec85d6db2b489b9829ba686e2e268d
Source dataset
uspto-grants-1987_09
Patent number
US04692552

Reaction notes

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