8-Acetyl-11-(1-hydroxycyclohexyl)undec-10-ynoic acid → 8-Acetyl-11-(1-hydroxycyclohexyl)undecanoic acid

HRID 839992Notes

Reaction equation

HRID 839992 reaction equation
[C:1]([CH:4]([CH2:14][C:15]#[C:16][C:17]1([OH:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:3])[CH3:2].C(C(CC#C[C@@H](O)CCCCC)CCCCCCC(O)=O)(=O)C>>[C:1]([CH:4]([CH2:14][CH2:15][CH2:16][C:17]1([OH:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 203222738-Acetyl-11-(1-hydroxycyclohexyl)undec-10-ynoic acidHCID 228010358-acetyl-12(S)-hydroxy-10-heptadecynoic acid

Product 1

HCID 203221898-Acetyl-11-(1-hydroxycyclohexyl)undecanoic acid

Procedure

This compound is prepared essentially by the same hydrogenation procedure described in Example 36, Step C, except that 8 -acetyl-11-(1-hydroxycyclohexyl)-10-undecynoic acid (Example 39) is substituted for 8-acetyl-12-(S)-hydroxy-10-heptadecynoic acid. The product is obtained as a yellowish viscous oil; pmr (CDCl3) δ 2.08 (3H,s CH3CO), δ6.52 (2H,s OH and COOH). Anal. Calcd. for C19H34O4 : C, 69.90; H, 10.50; Found: C, 70.23; H, 10.70.

Workup

  1. customThis compound is prepared essentially by the same hydrogenation procedure
  2. customThe product is obtained as a yellowish viscous oil

Sources & evidence

ORD record
ord-cbc23634db6149b2bd635563aace7a22
Source dataset
uspto-grants-1978_06
Patent number
US04097504

Reaction notes

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